Winter is a trans musician, storyteller, son, brother, and, less notably, Original Plumbing magazine’s Mr. Transman NYC 2013. Nicole is a non-trans journalist who writes about sexuality and gender and can remember a time not so long ago when every article about trans people or issues had to include an ad hoc definition of the term. Those days are gone, and in their place we have I Am Cait, part reality show, part PSA, a landmark moment for trans visibility, and a romp through the homes and closets of a very rich woman. Ahead, we discuss Sunday night's episode of Cait: "The Road Trip: Part Two."

Winter Laike: On last week’s episode of I Am Cait, Caitlyn’s new trans activist friends had a “girls’ night” and then took a road trip to San Francisco, where they met with trans women at the Human Rights Campaign. The trip was a way for Caitlyn to bond with other trans women and learn about the realities of life for trans people who are not rich celebrities.

Nicole Pasulka: I’m going to try to be less critical of Caitlyn this week. Queers and women can sometimes hold each other to an unfair standard. Being critical is our superpower. But we’re carrying all that misogynist baggage, too, and at the same time, we desperately want each other to be better than that. This show is talking not only about the nitty-gritty of gender dysphoria and transition, it’s taking on discrimination, bias crimes, and the struggles of women with way less privilege than Caitlyn. I can’t remember ever seeing a reality-TV star work this hard to understand the world outside her experiences. Plus, the ratings are terrible, so they must be doing something right.

W.L.: This episode begins at the HRC, where we left off last week. Laya Monarez tells the group about being violently attacked while doing survival sex work. Blossom Brown tells Cait that because she’s trans her application to nursing school has been rejected six times.

N.P.: I would like to be watching a reality-TV show about Blossom, honestly. In the car on the way back from the HRC office, Caitlyn acknowledges that she’s “lived a great life” and has a lot of advantages — mainly being white and rich. If this feels repetitive, it’s because the show has repeated it. A lot.

W.L.: The women reflect on the stories they heard from Blossom and Laya. Cait was moved by Blossom Brown’s story. So far, a number of people have brought up survival sex work, but Caitlyn hasn’t responded to these stories. So instead of discussing Laya, she is very focused on Blossom’s struggle, which is real, but it’s also not sex-work-focused.

Since Blossom loves Ellen DeGeneres, Cait wants to send the talk-show host an edit of her story and then pay for her to go to nursing school. Caitlyn Jenner just went from being the Barbara Walters of the trans community to being Oprah. You get tuition and a spot on Ellen! You get a job! Look under your seats; they’re your identification documents with an updated gender markeeeeeeeeer!

Chandi Moore sees a problem with Cait’s approach. “She has to work on one person at a time, and if she’s able to help that one somebody, then her work is done.” Blossom is one of thousands. How do you help all the women who have to do sex work to survive? Or are discriminated against by schools and jobs?

N.P.: This is so common, though. It’s the danger of using one person’s story to illustrate a larger issue. People read an article about a mother who’s dealing with food-stamp cuts and someone starts an Indiegogo campaign to help fix her house. A reporter writes a story about a man who walks 20 miles each way to work and reader donations buy him a new car. These are good people moved by inequality and poverty, but it’s so much easier to deal with a single person than an entire system.

W.L.: If writing a check is all that it takes to wipe out systematic oppression, will somebody please set up the Indiegogo account and preheat the oven for the bake sale?

NP: Back at the house, Caitlyn brings up changing her voice again. She hates that the way she talks could out her as trans. Candis Cayne hopes Cait can realize that “your voice is powerful — it’s who you are, it’s your identity.” Instead of forgetting the person you were, "you’re allowed to start from one place and end in another and not completely erase who you are." She manages to convey all the emotion and significance of “the voice” without any judgment.

On a Napa Valley patio with yet another a gorgeous view, Cait tells her friends she’s scared to present at the EPSY awards live in front of her whole family. When she goes back to her real life in Malibu, she’ll have to deal with the fact that she’s not on great terms with her kids. She so wants them to be “proud of their daddy.”

W.L.: This is the most vulnerable and sincere version of Cait that I have seen so far. She’s here with a group of women who really seem to value and understand each other. Jen Richards helps her choose a bathing suit, and her friends cheer as she finally gets the courage to join them in the pool. When you don’t have blood family that supports you, you can make your own chosen family.

N.P: And then take them dirt-bike-riding! They look so badass. Of course Chandi Moore is amazing at this.

W.L.: Finally, the ladies start to dish. Seated around the dinner table, they talk about which parts go where. Someone asks whether people like to date men or women. They all answer, “yes!” — except Jenny Boylan, who has only ever been interested in women. Caitlyn has never been with a man, but she appreciates the male form and isn’t completely closed off to the idea. Chandi doesn’t focus on the gender identity of a potential partner, but rather who they are as a person. Just as important as personality and ethics, Chandi says, “If they like Beyoncé, that’s a bonus.” More like, “If they don’t like Beyoncé, it’s a deal-breaker.”

N.P.: Ronda has been upset since episode two because Cait bosses her around and generally takes her for granted. She’s Caitlyn’s assistant, best friend, and primary support through transition, and now she’s jealous of all the love and good vibes Cait is sharing with the trans women on the trip. Ronda misses the intimacy she used to have with her boss. Oh, buddy, this is hard. Ronda feels bad that she’s down when Cait is clearly flying high, but Ronda does not feel bad enough to keep that to herself.

W.L.: It’s like you’ve just started high school and your best friend from junior high suddenly has a new group of friends. But when the vacation ends and your new trans BFFs go back to their everyday lives and your family is still not coming to visit you, who is going to be there by your side?

Ronda.

N.P.: Lucky for Ronda (and the rest of us), she’s at a Napa Valley villa with Jenny Boylan, who approaches the situation with the wisdom, humor, and compassion we’ve come to expect from J.Bo. Imagine Cait as a bride-to-be between the engagement and the wedding, Jenny suggests. She is euphoric because she’s living in a way that feels much truer to her sense of self, but she is also kind of awful to the people closest to her. Jenny manages to use the word transzilla without seeming the least bit judgmental, and a little later she tells Cait she’s been living in a “pink cloud.”

W.L.: I think it’s important for Cait not to exclude those people in her life who love and support her, especially at this stage in her transition. It’s already hard enough having to come out and transition in the public eye. It would be impossible without constant support along the way.

NP: At the vineyard, the women are welcomed by Sharon from Breathless Wines. Cait tells the others that she’s learned more from them than she has from anyone in her entire life — family excluded. Sharon comes back to say that watching Cait’s transition helped explain her father who “used to dress up and go to San Francisco in the '70s.” After watching Caitlyn Jenner, she now realizes that was him being free.

Winter, I want Cait to be the next Oprah, and all these women to produce the show.

W.L.: We went from beauty tips and obsessing over “the voice” to moving moment after moving moment. I don’t know how to handle this roller coaster of emotions.

N.P.: I’ve been waiting all episode for you to get emotional.

W.L.: [Bawls.]

N.P.: Cait and Candis leave the villa together. Ooooh. Oh. They’re heading out of the cozy “girls’ night” bubble and back to the real world — whatever that means for a member of the Kardashian family. In Malibu, she and Ronda smooth over some of the rough edges that have formed since her transition. If Cait’s going to face her family next episode, she’ll to need all the support she can get.

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